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Factfile: Gce Chemistry 5.7 Amines

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Factfile: Gce Chemistry 5.7 Amines FACTFILE: GCE CHEMISTRY 5.7 AMINES Amines Learning Outcomes 5.7.9 explain the colour of compounds such as dyestuffs and indicators based on the 5.7.1 recall the molecular and structural extent of delocalisation of electrons formulae of amines with up to six carbon leading to the closer proximity atoms, and refer to primary, secondary and of electronic energy levels. tertiary amines; 5.7.2 refer to the effect of hydrogen bonding on boiling point and miscibility with water; Amines 5.7.3 recall the formation of primary aliphatic amines by reduction of nitriles using lithium tetrahydridoaluminate(III) (lithal) and by the reaction of ammonia with alkyl halides; 5.7.4 explain the formation of phenylamine by reduction of nitrobenzene using tin and concentrated hydrochloric © Tony Craddock / Science Phot Library Craddock © Tony acid, to the phenylammonium The smell of fish is partly due to amines such as salt followed by liberation of the free ethylamine amine by addition of alkali; Amines are compounds based on ammonia, where 5.7.5 recall the formation of salts by the reaction hydrogen atoms have been replaced by alkyl or aryl of amines with mineral acids and the (C6H5-) groups Amines contain the —NH2 functional liberation of amines from their salts using group, which is called the amino group. They have alkali; a fishy smell. 5.7.6 explain the relative basic strengths of ammonia, primary, secondary, Naming tertiary aliphatic amines and phenylamine using the availability of the lone pair on There are different ways of naming amines – the nitrogen atom; usually just add –ylamine, or if there is a side 5.7.7 recall the reaction of amines with ethanoyl group it is often more convenient to name it by chloride and use this reaction to identify using amino. unknown amines; For example: NH 2 ethylamine 5.7.8 explain the formation of CH CH CH NH proplyamine (1-aminopropane) benzenediazonium chloride from 3 2 2 2 CH –CH–CH– phenylamine and recall the coupling of 3 3 diazonium ions with phenol and aniline; NH2 2-aminopropane H2NCH2CH2NH2 1,2–diaminiopropane C6H5NH2 phenylamine 1 FACTFILE: GCE CHEMISTRY / A2 5.7 AMINES A primary primary amine has only one carbon Secondary amines have lower boiling points – they directly bonded to the nitrogen atom and still form hydrogen bonds between molecules, but therefore has the NH2 group Examples include each N atom only has one H atom which can form hydrogen bonds with other molecules. NH2 CH3-NH2 CH3-CH2-NH2 CH3-CH2-CH2-NH2 CH3-CH-CH3 In a tertiary amine there aren’t any hydrogen atoms attached directly to the nitrogen. That A secondary amines has two carbon atoms means that hydrogen bonding between tertiary directly bonded to the nitrogen atom, amine molecules is impossible, the molecules only i.e For example: are held together by van der Waals’ forces and so NH the boiling points are much lower. H H 2. Solubility in water CH -N-CH CH -CH -N-CH -CH 3 3 3 2 2 3 Most primary amines can form hydrogen bonds dimethylamine diethylamine with water and so are soluble in water. hydrogen bond A tertiary amine has three carbon atoms directly CH O−H 3 bonded to the nitrogen atom i.e δ- H-N : H For example: N δ+ H CH 3 Solubility decreases as the hydrocarbon chains get CH -N-CH 3 3 longer - noticeably so after about 6 carbons. The trimethylamine hydrocarbon chains have to force their way between water molecules, breaking hydrogen bonds between The easiest way to recognise a primary, secondary water molecules. Secondary amines are less soluble or tertiary amine is to count the number of H atoms in water than primary amines and tertiary amines bonded to the N atom. are less soluble than secondary amines. 2 H atoms bonded to N atom – Primary amine e.g. Formation of primary aliphatic amines C H NH 2 5 2 1. by reduction of nitriles 1 H atom bonded to N atom – Secondary amine e.g. (nitriles contain the C N group) (C2H5)2NH 0 H atoms bonded to N atom – Tertiary amine e.g. Equation: CH3CH2CN +4 [H] → CH3CH2CH2NH2 (C2H5)3N propanenitrile propylamine Physical properties Condition: [H] is lithium tetrahydridoaluminate(III) 1. Boiling point (lithal) in ether at room temp Primary amines have a higher boiling point than the corresponding alkane because alkanes 2. by reaction of ammonia with halogenoalkanes only have weak van der Waals’ forces between molecules, but amines have strong hydrogen Equation: bromoethane + ammonia → bonds between the lone pair on the very ethylamine + hydrogen bromide electronegative nitrogen atom and the slightly CH CH Br + NH CH CH NH + HBr positive hydrogen atom in another molecule and 3 2 3→ 3 2 2 so more energy is needed to break these stronger o bonds and boil the amine. Condition: in a sealed glass tube at 100 C with excess ammonia hydrogen bond H H δ- δ+ CH3-N: H-N-CH: 3 - δ+H δ 2 FACTFILE: GCE CHEMISTRY / A2 5.7 AMINES Formation of phenylamine by reduction Relative basic strengths Usually compounds with a NH group are basic of nitrobenzene 2 because the lone pair of electrons on the nitrogen The protonated form of phenylamine, the atom can combine with a hydrogen ion (a proton) phenylammonium ion is first formed by the from some other source - it acts as a base (lone pair reduction of nitrobenzene with tin and concentrated donor/proton acceptor) hydrochloric acid. Concentrated sodium hydroxide then removes the hydrogen ion from the tertiary aliphatic amine phenylammonium salt liberating the free amine. secondary aliphatic amine basic primary aliphatic amine NO2 + 2H2O strength decreases phenylammonium ion ammonia primary aromatic amine + OH- NH + H O 2 2 amides phenylammonium ion phenylamine Conditions: [H] is tin and concentrated hydrochloric Primary aliphatic amines are stronger bases than acid. Heat under reflux, followed by addition of ammonia because of the alkyl group attached to concentrated sodium hydroxide solution. the nitrogen. The alkyl group is said to be electron donating – it releases electrons meaning there Overall the reduction is: is slightly more electron density on the nitrogen atom. As a result the lone pair is more available and so has an increased ability to accept a proton. NO + 6[H] Aliphatic amines generally increase in base 2 NH2 + 2H2O strength as the number of alkyl groups attached to nitrobenzene phenylamine the nitrogen atom increases. Reactions of amines as bases Primary aromatic amines are weaker bases than Amines are weak bases because the lone pair of ammonia because nitrogen’s lone pair of electrons electrons on the nitrogen atom can accept a proton. can overlap with the delocalised pi electrons in the benzene ring. The lone pair is delocalised into the amine + acid → alkylammonium salt pi system, the electron density on the nitrogen is decreased and the lone pair is less available for with dilute hydrochloric acid accepting a proton. Amides are weaker bases than primary aromatic amines (see 5.8) NH2 NH3Cl Reactions of Amines + HCl → With ethanoyl chloride phenylamine phenylammonium chloride ethanoyl chloride + propylamine→ N-propylethanamide + hydrogen chloride with dilute sulfuric acid CH COCl + CH CH CH NH → +CH CONHCH CH CH + HCl → 3 3 2 2 2 3 2 2 3 2CH3CH2NH2 + H2SO (CH3CH2NH3)2 SO4 ethylamine ethylammonium sulphate Conditions: room temp. Conditions: room temp The N in N-propylethanamide indicates that the propyl group is bonded to the nitrogen. To liberate the free amine from an amine salt add alkali and heat Use of this reaction. This reaction produces crystalline solids so the 3 FACTFILE: GCE CHEMISTRY / A2 5.7 AMINES reaction is used to identify an amine, by finding Coupling reaction of diazonium ions with phenol the melting point of the solid produced (after and aniline recrystallisation) and comparing to data books. Formation of benzene diazonium chloride A coupling reaction is a reaction in which two benzene rings are linked together through an Phenylamine reacts with nitrous acid to form azo (-N=N-) group benzene diazonium ion. Ionic equation: With phenol (C6H5OH) OH NH2 + + NaOH + + + HNO2+ H N N + 2H2O benzene diazonium ion N=N OH + NaCl + H2O Full equation: + - C6H5NH2 + HNO2 + HCl → C6H5N2 + Cl + 2H2O Conditions: cold NaOH Conditions: Nitrous acid (HNO2) decomposes very readily and is always made in situ from The dyes formed are called AZO DYES they hydrochloric acid and sodium nitrite solution. are yellow precipitates and often used as dyes or indicators. The one above is called NaNO2 + HCl → HNO2 + NaCl 4-hydroxyazobenzene. The temperature must be less than 5°C With aniline (phenylamine) In the benzene diazonium ion, make sure the + A yellow azo dye is produced. charge is placed on the nitrogen atom with four covalent bonds – it uses 4 electrons in forming 4 + covalent bonds and so has lost one electron N N + NH2 (N atom should have 5 electrons) and has a positive charge. + Note benzene diazonium chloride is unstable when N=N NH2 + H warmed and it reacts to form phenol. C6H5N2Cl + H2O → C6H5OH + N2 + HCl Why are dyestuffs and indicators coloured? For a compound to be coloured it has to remove Aliphatic amines react with nitrous acid to (absorb) one or more colours from white light. produce an alcohol and nitrogen – this is because If a molecule has a conjugated system or an aliphatic diaszonium ions are too unstable at any extended delocalised electron system – dyes and temperature. indicators do - this means that the energy levels are closer together and as a result less energy is CH3CH2NH2 + HNO2 → CH3CH2OH + N2 + H2O needed to cause an electron to be raised to a higher level.
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